Chapter 9 Benzene and Its Derivatives
Multiple Choice
1. Which structures have the correct IUPAC names? (Sec. 9.4)
CH3
CH3
Cl
Br
Br
I. 2-bromotoluene II. para methyl, meta chloro
bromobenzene
OCH3
NO2
Cl
CH2CH3
III. meta chloroaniline
a)
b)
c)
d)
IV. para ethylanisole
I, II
III, IV
I, IV
II, III
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Chapter 9 Benzene and Its Derivatives
2. Which of the named compounds have correct structures? (Sec. 9.4)
OH
O
CH3
Cl
CH2CH2 Br
I. meta chlorotoluene
Br
II. bromomethyltoluene
III. para bromophenol
NH2
OCH3
Cl
Cl
NO2
Cl
IV. ortho nitroanisole
a)
b)
c)
d)
V. 2,4,6-trichloroaniline
I, II, IV
I, III, IV
I, IV, V
II, III, V
3. How many Kekule structures are possible for naphthalene? (Sec. 9.2, 9.3)
a)
b)
c)
d)
3
4
5
6
4. How many -orbital electrons are in the following molecule? (Sec. 9.3)
N
N
H
a)
b)
c)
d)
4
6
8
10
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Chapter 9 Benzene and Its Derivatives
5. Which structures are aromatic? (Sec. 9.3)
O
O
N
O
III
IV
CH2
I
a)
b)
c)
d)
II
II, III
III, IV
I, III
II, IV
6. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)
OH
OH
OH
OH
NO2
I
a)
b)
c)
d)
Cl
NO2
NO2
II
III
IV
I, II, III, IV
III, II, IV, I
I, IV, III, II
II, III, IV, I
7. Arrange the compounds in order of increasing acidity (least first). (Sec. 9.9)
OH
OH
I
II
a)
b)
c)
d)
OH
O
OCH3
IV
III
I, II, III, IV
III, I, II, IV
IV, II, I, III
IV, II, III, I
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Chapter 9 Benzene and Its Derivatives
8. Arrange the compounds in order of increasing acidity (least first).
OH
(Sec. 9.9, 2.4)
OH
O
II
I
a)
b)
c)
d)
H2CO3
CH3COH
III
IV
I, II, III, IV
III, IV, II, I
I, II, IV, III
II, I, III, IV
9. How can phenol be distinguished from cyclohexanol? (Sec. 9.9, 8.3)
a)
b)
c)
d)
solubility in water
solubility in hydrochloric acid solution
solubility in sodium bicarbonate solution
solubility in sodium hydroxide solution
10. How many mono-bromoanthracenes are possible? (Sec. 9.2, 9.3)
a)
b)
c)
d)
1
2
3
4
11. Which contributing resonance structure is the most important for the bromination of anisole? (Sec. 9.8)
OCH3
a)
OCH3
b)
H
Br
OCH3
c)
H
Br
OCH3
d)
H
Br
12. Which is the electrophile in the nitration of benzene? (Sec. 9.7)
a) HNO3
b) NO2
c) NO3
d) NO
103
H
Br
Chapter 9 Benzene and Its Derivatives
13. Which compound reacts most readily in the nitration reaction? (Sec. 9.7)
CH3
CH3
a)
b)
CH3
c)
OCH3
HNCCH3
CH3
d)
COH
SO3H
O
O
14. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first). (Sec. 9.7)
O
O
CNHCH3
NH2
NO2
I
II
III
a)
b)
c)
d)
HNCCH3
IV
II, I, IV, III
I, III, IV, II
III, I, IV, II
IV, III, II, I
15. Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution
(lowest first). (Sec. 9.7)
CH3
Cl
OH
I
II
III
O
IV
a) III, II, I, IV
b) IV, II, I, III
c) III, I, II, IV
d) I, II, III, IV
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Chapter 9 Benzene and Its Derivatives
16. Which is the major product of the following reaction? (Sec. 9.6)
OCH3
O
NO2
H3CCCl
AlCl3
O
OCH3
OCH3
NO2
NO2
a)
OCH3
b)
OCH2CCH3
NO2
c)
d)
CCH3
H3CC
O
O
CCH3
O
17. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
O
HC
Br2
CH2
FeBr3
O
O
HC
HC
CH2
a)
CH2
b)
Br
Br
O
O
HC
c)
HC
CH2
Br
d)
CH2
Br
105
NO2
Chapter 9 Benzene and Its Derivatives
18. Which is the major product of the following series of reactions? (Sec. 9.5, 9.8)
CH3
AlCl3
K2Cr2O7
H3CCCl
H2SO4
O
O
O
O
COH
CCH3
CCH3
a)
b)
c)
OCH3
d)
COH
COH
CCH3
COH
O
O
O
O
19. Which is the best reaction sequence for preparing the following compound from benzene?
(Sec. 9.6, 9.8)
O
COH
NO2
a)
AlCl3
CH3Cl
K 2Cr2O7
H2SO 4
b)
HNO 3
H2SO 4
AlCl3
CH3Cl
c)
AlCl3
H3CCl
HNO 3
H2SO4
d)
O
AlCl3
CH3Cl
HNO3
H2SO 4
HNO3
H2SO4
K 2Cr2O7
H2SO4
K2Cr2O 7
H2SO4
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Chapter 9 Benzene and Its Derivatives
20. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
O
O
CCH2CH2CCl
AlCl3
O
a)
b)
O
O
c)
d)
O
21. Which is the electrophile in the final reaction step for the following reaction? (Sec. 9.7)
O
OH +
CH3
H3PO4
HO
H3CCCH3
C
OH
CH3
CH3
a) HO
CCH3
b) HO
C
CH3
O
c) HO
C
OH
d)
H3CCCH3
22. Which is the major product of the following reaction? (Sec. 9.6, 9.8)
HNO3
H2SO4
a)
b)
c)
d)
Cl2
FeCl3
1-chloro-4-nitrobenzene
1-chloro-3-nitrobenzene
1-chloro-2-nitrobenzene
a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene
107
OH
Chapter 9 Benzene and Its Derivatives
23. Which is the major product of the following reactions? (Sec. 9.6, 9.8)
HNO3
H2SO4
CH2
Br
Br2
FeBr3
Br
NO2
a)
CH2
CH2
b)
NO2
NO2
c)
Br
CH2
NO2
d)
Br
24. Which is the major product of the following reactions? (Sec. 9.5, 9.6, 9.8)
CH3Cl
FeCl3
Cl2
FeCl3
a)
b)
c)
d)
K2Cr2O7
H2SO4
para chlorobenzoic acid
meta chlorobenzoic acid
a mixture of para and meta chlorobenzoic acid
a mixture of ortho and para chlorobenzoic acid
25. Which is the electrophile in the following reaction? (Sec. 9.7)
H3PO4
+
a)
b)
c) HPO3
108
d)
CH2
Chapter 9 Benzene and Its Derivatives
Fill in the Blank
1. The major product of the following reaction is,
OH
H3PO4
(Sec. 9.6, 9.8)
2. The major product of the following reaction is,
K2Cr2O7
H2SO4
(Sec. 9.5)
3. The major product of the following reaction is,
O
Br
Cl
AlCl3
(Sec. 9.6, 9.8)
4. The major products of the following reaction are,
OH
OH
NaOH
+
H2O
(Sec. 9.9)
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Chapter 9 Benzene and Its Derivatives
5. The major products of the following reaction are,
O
OH
OH
NaHCO3
+
H2O
(Sec. 9.9)
6. The reagent that completes the following reaction is,
CH3
CH3
NO2
(Sec. 9.6, 9.8)
7. The reagents that complete the following reactions are,
SO3H
8. The starting material and reagent that complete the following reaction are,
SO3H
Cl
110
(Sec. 9.6, 9.8)
(Sec. 9.6, 9.8)
Chapter 9 Benzene and Its Derivatives
9. The reagents and mid-reaction product that complete the following scheme are,
Cl
O
(Sec. 9.6, 9.8)
10. The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,
Br
+
H
C
+
Br
Br
H
(Sec. 9.7)
True-False
1. The name of the following structure is 2,4-diethylnitrobenzene. (Sec. 9.4)
NO2
2. The name of the following structure is 3,5-dibromobenzoic acid. (Sec. 9.4)
O
Br
OH
Br
3. The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene.
(Sec. 9.6, 9.8)
4. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone. (Sec. 9.5)
5. The product of the reaction of benzoic acid and chlorine/AlCl 3 is m-chlorobenzoic acid. (Sec. 9.6, 9.8)
111
Chapter 9 Benzene and Its Derivatives
6. The following compound is aromatic. (Sec. 9.3)
7. The following reaction scheme will synthesize the product shown. (Sec. 9.5, 9.6, 9.8)
OH
O
CH3CH2Cl
AlCl3
K2Cr2O7
Br2
H2SO4
FeBr3
Br
8. The following reaction scheme will synthesize the product shown. (Sec. 9.6, 9.8)
SO3H
SO3
CH3CH2Cl
H2SO4
AlCl3
9. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution. (Sec. 9.7)
OH
CH3
>
SO3 H
>
>
10. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic
substitution. (Sec. 9.7)
Cl
O
NO2
>
>
>
112
Chapter 9 Benzene and Its Derivatives
Answers
Multiple Choice
1. c
2. c
3. a
4. b
5. c
6. a
7. c
8. a
9. d
10. c
11. d
12. b
13. b
14. c
15. b
16. b
17. c
18. b
19. d
20. d
21. a
22. b
23. c
24. d
25. b
Fill in the Blank
1.
2.
O
OH
113
Chapter 9 Benzene and Its Derivatives
3.
Br
O
4.
O
OH
+
5.
O
O
OH
+
6. HNO3, H2SO4
7.
Cl
SO3, H2SO4
AlCl3
8.
Cl
SO3 , H2SO4
114
Chapter 9 Benzene and Its Derivatives
9.
O
Cl
O
Cl2 , FeCl3
AlCl3
10.
Br
+
H
C
+
Br
Br
H
True-False
1. T
2. T
3. F
4. F
5. T
6. F
7. F
8. T
9. T
10. F
115